DE69601165T2 - Nebenprodukt reinigung bei der herstellung von polyestern auf der basis von 1,3-propandiol - Google Patents
Nebenprodukt reinigung bei der herstellung von polyestern auf der basis von 1,3-propandiolInfo
- Publication number
- DE69601165T2 DE69601165T2 DE69601165T DE69601165T DE69601165T2 DE 69601165 T2 DE69601165 T2 DE 69601165T2 DE 69601165 T DE69601165 T DE 69601165T DE 69601165 T DE69601165 T DE 69601165T DE 69601165 T2 DE69601165 T2 DE 69601165T2
- Authority
- DE
- Germany
- Prior art keywords
- solution
- acrolein
- aqueous
- base
- basic solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Revoked
Links
- 229920000728 polyester Polymers 0.000 title claims description 16
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 title claims description 14
- 239000006227 byproduct Substances 0.000 title description 34
- 238000004519 manufacturing process Methods 0.000 title description 6
- 238000004140 cleaning Methods 0.000 title 1
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims description 78
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 57
- 239000000243 solution Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 22
- 239000002585 base Substances 0.000 claims description 19
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 13
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000003637 basic solution Substances 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 3
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 29
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000010802 sludge Substances 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 238000007865 diluting Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 230000036284 oxygen consumption Effects 0.000 description 3
- -1 poly(propylene terephthalate) Polymers 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000002028 Biomass Substances 0.000 description 2
- 229920001634 Copolyester Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 238000012643 polycondensation polymerization Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/183—Terephthalic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/88—Post-polymerisation treatment
- C08G63/90—Purification; Drying
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyesters Or Polycarbonates (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/395,231 US5459229A (en) | 1995-02-27 | 1995-02-27 | By product stream purification in the preparation of 1,3-propanediol-based polyesters |
PCT/EP1996/000809 WO1996026970A1 (en) | 1995-02-27 | 1996-02-26 | Byproduct stream purification in the preparation of 1,3-propanediol-based polyesters |
Publications (2)
Publication Number | Publication Date |
---|---|
DE69601165D1 DE69601165D1 (de) | 1999-01-28 |
DE69601165T2 true DE69601165T2 (de) | 1999-06-10 |
Family
ID=23562194
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE69601165T Revoked DE69601165T2 (de) | 1995-02-27 | 1996-02-26 | Nebenprodukt reinigung bei der herstellung von polyestern auf der basis von 1,3-propandiol |
Country Status (17)
Country | Link |
---|---|
US (1) | US5459229A (xx) |
EP (1) | EP0812337B1 (xx) |
JP (1) | JP3415848B2 (xx) |
KR (1) | KR100398820B1 (xx) |
CN (1) | CN1074428C (xx) |
AR (1) | AR001015A1 (xx) |
AT (1) | ATE174608T1 (xx) |
AU (1) | AU689378B2 (xx) |
BR (1) | BR9607389A (xx) |
DE (1) | DE69601165T2 (xx) |
ES (1) | ES2125718T3 (xx) |
MY (1) | MY113798A (xx) |
PL (1) | PL321965A1 (xx) |
TR (1) | TR199700855T1 (xx) |
TW (1) | TW376393B (xx) |
WO (1) | WO1996026970A1 (xx) |
ZA (1) | ZA961511B (xx) |
Families Citing this family (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5527973A (en) * | 1994-12-16 | 1996-06-18 | Kelsey; Donald R. | Purification of 1,3-propanediol |
DE19705249A1 (de) * | 1997-02-12 | 1998-08-13 | Zimmer Ag | Verfahren zur Herstellung von Polypropylenterphthalat |
MY118950A (en) * | 1997-04-30 | 2005-02-28 | Shell Int Research | Purification of by- product stream in preparation of polytrimethylene terephthalate |
US6245844B1 (en) * | 1998-09-18 | 2001-06-12 | E. I. Du Pont De Nemours And Company | Nucleating agent for polyesters |
US6245879B1 (en) * | 1999-01-29 | 2001-06-12 | Shell Oil Company | Purification of 1,3-propanediol in carbonyl-containing stream |
US5989665A (en) * | 1999-03-15 | 1999-11-23 | Eastman Chemical Company | Copolyesters of 1,3-propanediol having improved gas barrier properties |
US6350895B1 (en) | 1999-03-26 | 2002-02-26 | E. I. Du Pont De Nemours And Company | Transesterification process using yttrium and samarium compound catalystis |
US6331264B1 (en) | 1999-03-31 | 2001-12-18 | E. I. Du Pont De Nemours And Company | Low emission polymer compositions |
US6512080B2 (en) | 1999-04-22 | 2003-01-28 | Shell Oil Company | Process of producing polytrimethylene terephthalate (PTT) |
EP1046662B1 (en) * | 1999-04-22 | 2003-03-12 | Zimmer Aktiengesellschaft | Process of producing polytrimethylene terephthalate (PTT) |
US6277947B1 (en) | 2000-04-21 | 2001-08-21 | Shell Oil Company | Process of producing polytrimethylene terephthalate (PTT) |
US6277289B1 (en) | 1999-07-01 | 2001-08-21 | E. I. Du Pont De Nemours And Company | Treatment of aqueous aldehyde waste streams |
US6284930B1 (en) | 1999-07-30 | 2001-09-04 | E.I. Du Pont De Nemours And Company | Process for the preparation of 3-hydroxypropanal |
EP1208130B1 (en) | 1999-08-25 | 2005-03-02 | E.I. Du Pont De Nemours And Company | Preparation of poly(trimethylene terephthalate) |
US6436503B1 (en) | 1999-09-08 | 2002-08-20 | General Electric Company | Data storage medium containing polyestercarbonate |
US6410619B2 (en) | 1999-11-22 | 2002-06-25 | Bayer Corporation | Method for conditioning organic pigments |
US6353062B1 (en) * | 2000-02-11 | 2002-03-05 | E. I. Du Pont De Nemours And Company | Continuous process for producing poly(trimethylene terephthalate) |
WO2001058981A1 (en) * | 2000-02-11 | 2001-08-16 | E.I. Du Pont De Nemours And Company | Continuous process for producing poly(trimethylene terephthalate) |
US6528579B2 (en) | 2000-02-17 | 2003-03-04 | Shell Oil Company | Zero-heel polyester process |
GB2361925A (en) | 2000-05-02 | 2001-11-07 | Shell Internat Res Maatschhapp | High temperature solid state polymerisation of poly(trimethylene terephthalate) |
US6576774B2 (en) * | 2000-07-20 | 2003-06-10 | Shell Oil Company | Process for recycling polytrimethylene terephthalate cyclic dimer |
US6403762B1 (en) | 2000-08-21 | 2002-06-11 | Shell Oil Company | Solid state polymerization process for poly(trimethylene terephthalate) utilizing a combined crystallization/preheating step |
US6600061B1 (en) | 2000-11-15 | 2003-07-29 | General Electric Company | Method for the continuous production of aromatic carbonates |
DE10125677B4 (de) * | 2001-05-25 | 2013-05-16 | Lurgi Zimmer Gmbh | Verfahren und Vorrichtung zur Herstellung von Polytrimethylenterephthalat |
EP1347005A1 (en) * | 2002-03-23 | 2003-09-24 | Zimmer AG | Polytrimethylene terephtalate resins with improved properties |
US20040222154A1 (en) * | 2003-05-08 | 2004-11-11 | E.I.Du Pont De Nemours & Company | Treatment of non-aqueous aldehyde waste streams |
DE102005017428A1 (de) * | 2005-04-15 | 2006-10-19 | Zimmer Ag | Verfahren zur kontinuierlichen Herstellung von Polyoxitrimethylenglykol-Polytrimethylenterephthalat-Copolyestern |
US20070149756A1 (en) * | 2005-12-26 | 2007-06-28 | Futura Polyesters Limited | Compositions and methods of manufacturing polytrimethylene naphthalate |
CN104987497A (zh) * | 2015-07-20 | 2015-10-21 | 福建师范大学泉港石化研究院 | 一种过柱去除聚酯多元醇中酸值的方法 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4096122A (en) * | 1972-03-18 | 1978-06-20 | Dynamit Nobel Aktiengesellschaft | Process for the production of polyesters of 1,4-butanediol |
US4014858A (en) * | 1975-05-12 | 1977-03-29 | Standard Oil Company | Polybutylene terephthalate |
US4375538A (en) * | 1980-12-22 | 1983-03-01 | Monsanto Company | Polymer compositions comprising adducts of acrolein and isocyanuric acid |
US4611049A (en) * | 1984-06-07 | 1986-09-09 | Teijin Limited | Process for producing aromatic polyester |
DE3422733A1 (de) * | 1984-06-19 | 1985-12-19 | Teijin Ltd., Osaka | Verfahren zur herstellung von aromatischen polyestern |
JP2976500B2 (ja) * | 1990-08-27 | 1999-11-10 | 東洋紡績株式会社 | 樹脂粒子およびその製造方法 |
US5340909A (en) * | 1991-12-18 | 1994-08-23 | Hoechst Celanese Corporation | Poly(1,3-propylene terephthalate) |
JP2758525B2 (ja) * | 1992-02-12 | 1998-05-28 | ポリプラスチックス株式会社 | 改質ポリエステル |
-
1995
- 1995-02-27 US US08/395,231 patent/US5459229A/en not_active Expired - Lifetime
-
1996
- 1996-02-16 MY MYPI96000596A patent/MY113798A/en unknown
- 1996-02-23 AR ARP960101493A patent/AR001015A1/es unknown
- 1996-02-26 AU AU49427/96A patent/AU689378B2/en not_active Ceased
- 1996-02-26 TR TR97/00855T patent/TR199700855T1/xx unknown
- 1996-02-26 DE DE69601165T patent/DE69601165T2/de not_active Revoked
- 1996-02-26 PL PL96321965A patent/PL321965A1/xx unknown
- 1996-02-26 ES ES96905815T patent/ES2125718T3/es not_active Expired - Lifetime
- 1996-02-26 BR BR9607389A patent/BR9607389A/pt not_active Application Discontinuation
- 1996-02-26 CN CN96192183A patent/CN1074428C/zh not_active Expired - Fee Related
- 1996-02-26 AT AT96905815T patent/ATE174608T1/de not_active IP Right Cessation
- 1996-02-26 WO PCT/EP1996/000809 patent/WO1996026970A1/en not_active Application Discontinuation
- 1996-02-26 KR KR1019970705888A patent/KR100398820B1/ko not_active IP Right Cessation
- 1996-02-26 JP JP52601796A patent/JP3415848B2/ja not_active Expired - Fee Related
- 1996-02-26 ZA ZA961511A patent/ZA961511B/xx unknown
- 1996-02-26 EP EP96905815A patent/EP0812337B1/en not_active Revoked
- 1996-03-06 TW TW085102736A patent/TW376393B/zh not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
AU4942796A (en) | 1996-09-18 |
TR199700855T1 (xx) | 1998-02-21 |
PL321965A1 (en) | 1998-01-05 |
CN1074428C (zh) | 2001-11-07 |
ZA961511B (en) | 1996-09-03 |
US5459229A (en) | 1995-10-17 |
EP0812337B1 (en) | 1998-12-16 |
DE69601165D1 (de) | 1999-01-28 |
ES2125718T3 (es) | 1999-03-01 |
WO1996026970A1 (en) | 1996-09-06 |
TW376393B (en) | 1999-12-11 |
AR001015A1 (es) | 1997-08-27 |
ATE174608T1 (de) | 1999-01-15 |
CN1178539A (zh) | 1998-04-08 |
KR100398820B1 (ko) | 2004-02-05 |
KR19980702488A (ko) | 1998-07-15 |
JP3415848B2 (ja) | 2003-06-09 |
MX9706480A (es) | 1997-11-29 |
BR9607389A (pt) | 1997-11-25 |
EP0812337A1 (en) | 1997-12-17 |
AU689378B2 (en) | 1998-03-26 |
MY113798A (en) | 2002-05-31 |
JPH11501060A (ja) | 1999-01-26 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
8363 | Opposition against the patent | ||
8331 | Complete revocation |